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<h1><a href="https://archiveofourown.org/works/22743328">The Boss' Punishment</a> by <a class='authorlink' href='https://archiveofourown.org/users/Hot_Vanilla_Cream/pseuds/Hot_Vanilla_Cream'>Hot_Vanilla_Cream</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Monster Prom (Visual Novel)</td></tr>

<tr><td><b>Genre:</b></td><td>Begging, Crotch Stepping, Degradation, Dirty Talk, Dom/sub, F/F, Femdom, Hair-pulling, Humiliation, POV Second Person, Plot What Plot/Porn Without Plot, Rough Sex, Safe Sane and Consensual, Scratching, Self-Indulgent, Self-Insert, Sexual Roleplay, Strap-Ons, Teasing</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-02-16</td></tr>

<tr><td><b>Updated:</b></td><td>2020-02-16</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-04-28 08:46:38</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>Creator Chose Not To Use Archive Warnings</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>4,174</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/22743328</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/Hot_Vanilla_Cream/pseuds/Hot_Vanilla_Cream</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>You messed with the wrong gorgon, and now you need to be punished.</p><p>(Or: I just want to fuck Vera Oberlin, okay?)</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Vera Oberlin/Self-Insert</td></tr>

<tr><td><b>Comments:</b></td><td>3</td></tr>

<tr><td><b>Kudos:</b></td><td>71</td></tr>

</table>

<a name="section0001"><h2>The Boss' Punishment</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>ive written dumb self indulgent stuff before but this is. the first time ive written porn thats basically me/[character i have a crush on]. i originally thought i would do somethin like this with megurine luka (which i technically did on my main but that wasnt Full On Smut) so this is uh. A Trip</p><p>also brief tw for use of the d slur bc im. a useless lesbian</p>
    </blockquote></div><div class="userstuff module">
    
    <p>"Well, well, well," she hummed, glaring down at you. "What do you think you're doing here?"</p><p>You shuddered, trying to hide the enjoyable flush her tone sent to your face. You had been dating Vera for some time now, but the way her voice lowered whenever she was trying to seduce you never failed to turn you on. She knew all your weak points, it seemed, but you didn't mind. It made you feel vulnerable in the best possible way.</p><p>"N-nothing, Boss," you stammered, shoving the item in your hands behind your back. "I was just, uh...looking for you. I wanted to tell you about, um..." Your voice trailed off as you failed to think of a good excuse. Not that it mattered, of course. You both know you didn't really do anything wrong; it was all part of the game. Getting "caught" was only the first step.</p><p>"As incredible as I am, I can't fit inside a bedside drawer," she muttered darkly, eyes fixated on your arms. "Unless...it wasn't me you were looking for?" Her mouth curled into a devilish grin as she watched you squirm in place.</p><p>"Wh-what are you talking about, Boss?" you asked, your voice rising to a slightly higher pitch. "Of course I was looking for you. I was just-"</p><p>"Snooping through my things." She took a step forward, glaring menacingly into your eyes. "What's that you have behind your back there? If you <em>really</em> weren't snooping, you wouldn't be hiding anything that belongs to me, would you?" Her voice was sickeningly sweet, sending a chill down your spine. Your eyes darted downward, away from hers, only for her to grab your face and force you to look at her again. "<em>Would you?</em>"</p><p>Your breath hitched for a moment as you stared into her cold red eyes. Despite the mask of anger she wore, you could tell with just one glance that she was definitely getting some kind of pleasure out of treating you this way. You would be lying if you said you didn't find it arousing yourself.</p><p>"Well?"</p><p>You jolted back to reality and remembered the object behind your back. Slowly, shame burning in your stomach, you held it out to her, and this time she didn't reprimand you for avoiding her gaze.</p><p>"Oh, my." Her tongue, forked like the snakes that adorned her head, flicked out across her lips. "Is that what got your attention? Out of all the things in there, you chose this?"</p><p>You clenched your legs together, shuffling them to stifle the wetness that was beginning to build between them. "It's not what it looks like, Boss, I swear! I was...I was looking for something else-"</p><p>Vera seized upon your words like a cat to a mouse. "Oh, really? Because I'm pretty sure that was my <em>naughty drawer</em> you were just sifting through."</p><p>You gasped, pretending to be shocked. In reality, you knew perfectly well what drawer you were looking in, as the two of you had bought its contents together. But for the sake of the game, you acted like you had no idea.</p><p>"I-i didn't know, Boss, honest! Like I said, I was looking for something else-"</p><p>"Aha!" she interrupted. "So you admit you were going through my private things!"</p><p>Your mouth snapped shut, as you were unable to come up with a counter. Instead, you nodded shamefully, wincing as her lips nearly brushed against yours.</p><p>"Nobody disrespects me and gets away with it," she hissed - literally. The snakes on her head joined her, leaning toward your ears to remind you just how much trouble you were in. "Get on your knees."</p><p>Without thinking, you obeyed, pure submissive instinct taking control over your body. You looked up at Vera, the edges of her mouth raised in a triumphant grin, the leather jacket that she knew you loved popped open to reveal her low-cut shirt. She looked so tall when you were on your knees in front of her, power radiating from her stance.</p><p>"That was quick," she snickered. A pale green hand extended toward you, and you obediently give her the strap-on, heat once again rising to your cheeks. "I'll take that. I think I'll save it for later, what about you?" You opened your mouth to respond, but she cut you off. "That was rhetorical. I'm totally going to fuck you with it."</p><p>The bluntness of her statement was enough to send another jolt between your legs. You tried to clench them shut again, but she stopped you with a high-heeled shoe on your crotch.</p><p>"Aw, does that excite you?" she jeered, mockingly digging her foot into you. "Did you do this just to get my attention? So you could fulfill some sick, perverted fantasy?"</p><p>"B-boss-"</p><p>You felt a sharp tug on your hair, and her foot pressed harder against your crotch. The combined sensation was enough to get you to let out a high, breathless moan as you stared at Vera helplessly.</p><p>"I'm not your 'boss,'" she growled. "I'm your <em>master.</em> Say it."</p><p>Your words were stilted, occasionally interrupted by shuddering gasps, but you managed to let out a, "Yes, Master," before she let go of your hair. Her foot stayed right where it was, though, pressing down hard against your slit through the thin fabric of your pants.</p><p>"Just as I thought." She sighed and shook her head dramatically. "Honestly, I should have suspected you were a little freak. I know the kind of weird porn you get off to." Your eyes must have widened, because she smirked down at you with a chuckle. "What, you think I don't know? I know everybody's fetishes. They make for great blackmailing material."</p><p>If you weren't so incredibly aroused, you probably would have laughed. You were partially responsible for helping her discover what some of your friends were into. Of course, you were basically required to tell her what you liked as well, since she needed a way to "keep you in line" in case you ever betrayed her. Not that you minded, obviously - you were already doing all sorts of freaky shit with her at that point.</p><p>"You like this shit, don't you?" she asked, her heel pressing down against your entrance. "Being dominated. Being stepped on. Being called a <em>slut.</em>"</p><p>You moaned, hoping she would take that as confirmation, but she dug into you harder and forced another "Yes, Master," from your lips. Unconsciously, your hips bucked toward her foot, a spark of pleasure shooting through your core at the harsh sensation it sent to your crotch.</p><p>"Well, you're definitely acting like a slut right now," she taunted. "Look at you, grinding against me like that. All because I'm stepping on you! And that's not even the most extreme thing you're into, isn't it?"</p><p>"N-no, Master."</p><p>"Just think," she continued, as if you hadn't spoken, "I could be doing all kinds of messed-up stuff to you right now." She bent down to get closer to your face, looking you directly in the eyes. "If I wanted to, I could have you tied up on my bed, begging through a pretty little gag for me to let you cum. You'd like that, wouldn't you?"</p><p>Your mind swirled with the image she had described, and you felt your clit throb with anticipation. "<em>God,</em> yes, Master," you replied, almost dizzy with want.</p><p>Vera laughed, an uncommon sound, but one you treasured nonetheless. "You really are a whore, aren't you?" she purred. "I can get you to do anything with my foot on your crotch like this." She put a hand to her chin in thought before you saw her eyes glint with malice. "How about this: since I'm <em>so</em> generous, I'll let you off with a light punishment this time. How does that sound?"</p><p>You nodded eagerly. Light or not, you still wanted to be punished, and you knew from experience that Vera could come up with some pretty twisted methods of disciplining you.</p><p>"Take off your clothes," she ordered, and you obeyed in a heartbeat.</p><p>You practically tore off your shirt, throwing it to the side of the room like it was on fire, and yanked your pants off the second she lifted her foot for you to do so. You were about to remove your bra when she shook her head.</p><p>"Not yet," she said. "Just hold on one second." </p><p>Before you could ask what she was doing, you let out a high-pitched whimper as she left one harsh, final step to your crotch that left you seeing stars. She grinned in satisfaction. "Okay, you can take them off now."</p><p>Dazed and breathless, you removed your undergarments and gazed up at Vera with wide, hungry eyes. She looked so irresistible in that outfit, and it was so unfair that she was still fully clothed while you were stark naked. Still, you kept quiet, waiting for her next order and keeping your legs spread ever so slightly.</p><p>Vera's smile grew even more malicious as she reached into the pocket of her jacket and pulled out her phone. You felt your heart practically leap into your throat, accompanied by a twinge of nervousness, but you didn't say the safeword. You wanted to see where this was going, and if your suspicions were correct, you felt like you were going to like it.</p><p>Vera tapped at her phone a few times before holding it upright with a devious glint in her eyes. "Now," she began, "repeat after me: 'I'm Mistress Vera's obedient little slut.'"</p><p>Your heart skipped a beat as you realized she was <em>recording</em> you, no doubt making sure the camera captured every detail of your nude body. And yet, somehow, the thought was too exciting for you to say no.</p><p>"I'm Mistress Vera's obedient little slut," you repeated, your voice trembling with arousal. Behind the phone, Vera smirked.</p><p>"Now say 'I love being a slave to Mistress Vera's cock.'"</p><p>"I love being a slave to Mistress Vera's cock," you said, your eyes briefly glancing over at the strap-on still dangling from her hand.</p><p>"'I want Vera to fuck me senseless.'"</p><p>"I want Vera to fuck me senseless."</p><p>"'I want Vera to use me like a pathetic toy.'"</p><p>"I want Vera to use me like a pathetic toy."</p><p>Finally, she chuckled darkly, looking directly at you over her phone. "Now: 'I'm a stupid, useless dyke.'"</p><p><em>Oh,</em> fuck, you thought, your face reddening even more. You felt your clit throb a bit as you said the next words. "I-i'm...I'm a stupid, useless dyke."</p><p>"'And the only thing I'm good for is eating pussy,'" she concluded, a note of satisfaction in her tone.</p><p>"And the only thing I'm good for is eating pussy," you finished. You watched as Vera tapped her phone, presumably stopping the recording. Your eyes widen as she turned the screen toward you, playing the whole thing back for you to watch.</p><p>"What do you think?" she asked, clearly enjoying the look on your face. "I think the camera suits you. Look, you barely even hesitated when I told you to say those things!"</p><p>You hardly acknowledged her words as you stared, transfixed, at the video. You looked so vulnerable and yet so eager, so small yet so full of conviction. Most importantly, however, was the not-so-subtle glint of the juices that dripped down your inner thighs. Either Vera's phone camera had extremely good quality, or you were very, <em>very</em> wet. And the damp, sticky sensation between your legs told you exactly what you needed to know.</p><p>"Now," Vera started, snapping you out of your daze, "who should I send this to?"</p><p>Your head shot up, eyes wide. "Wh-what?!"</p><p>"You heard me," she responded, almost cheerfully. "Who should I send this video to? Miranda, Polly, Amira? Don't think I don't see the eyes you make at her in class." She gasped, as if a lightbulb had gone off over her head. "Ooh, what about Dahlia? I know how much you admire those big muscles of hers. What would she think if she saw you like this?"</p><p>For a moment, you knelt there, frozen in shock. And yet, despite your humiliation, the safeword was the furthest thing from your mind. Instead, your head was filled with all kinds of scenarios: Vera and Dahlia teasing you for being such a shameless slut, Vera filming you while Dahlia pinned you down and fingered you, Vera and Dahlia, Vera and Dahlia...</p><p>"Looks like you really like that," she remarked, snapping you out of your daydreams. "Dahlia it is, then! On the count of three, I'll send it to her, so if you want me to stop, now's your chance to say something." She glanced at you for approval, and you found that, despite the embarrassment coursing through your veins, you had no objections.</p><p>"One..."</p><p>You held your breath, sitting up as straight as you could. Still no objections.</p><p>"Two..."</p><p>You closed your eyes, trying to ignore the needy throbbing of your cunt as you braced yourself.</p><p>Then, laughter.</p><p>"<em>Ahahahaha!</em>" erupted Vera, shutting off her phone. "Yeah, right! You should have seen the look on your face!"</p><p>You blinked, a wave of realization hitting you like a slap to the face. She...wasn't going to send the video to Dahlia? You paused, your brain processing all of this information, before letting out some laughter of your own. Before long, the two of you were laughing together, the sensual atmosphere temporarily forgotten as you both realized the humor of the situation.</p><p>"What, you think I would just send something like that to someone else? As much as Dahlia likes you, I don't think she'd want to randomly get a video of you naked," Vera said, her laughter dying down a bit. "Besides, consent is important. I may be a crime boss, but I still have <em>some</em> morals."</p><p>You finished your bout of giggles, nodding at her words. As hot as the thought of a threesome between the two of you and Dahlia was, you knew Vera wouldn't be as willing to share you so easily. Maybe some other time, but not now. Now, you belonged to her, and her alone.</p><p>"Anyway," Vera said, her voice lowering once again, "I think you've learned your lesson. For that, I'd say you deserve a reward."</p><p>Your head shot toward her, a hopeful expression on your face. Briefly, you looked over at the strap still in her hand, and she smiled at you reassuringly.</p><p>"Yes, yes, I'll be using the toy you picked out. It's only fair, isn't it?" For a moment, the malicious glint returned to her eyes. "And you should be grateful that I've decided to be fair for once."</p><p>The mesmerizing stare she was giving you caused a wave of submission to wash over you. In an instant, you were reminded of how much power she had, and you felt that familiar urge to be obedient to her rise within you.</p><p>"Yes, Master. Thank you, Master," you said, bowing your head to her. She seemed to like that a lot, as she briefly placed a hand on your head to run through your hair.</p><p>"Good girl," she praised. "Now, take off my clothes for me."</p><p>You complied, your hands trembling when she turned around for you to pull off the leather jacket. Instead of tossing it to the other side of the room like you did with your own clothes, you instead opted to carefully place it on the bed. You did the same with her shirt and bra, only pausing to stare at her sizable breasts.</p><p>"You want to touch them, don't you?" she asked with a knowing look. "Go ahead. But don't spend too much time on them."</p><p>"Thank you, Master." Gingerly, you reached out to caress her breasts, your fingers circling around the already hardened nipples with expertise. You had done this before, so you knew exactly what to do to pleasure her.</p><p>Vera sighed contentedly and let you do your thing, draping a tender hand over the back of your neck. You gently pinched her nipples before wrapping your lips around one of them and sucking. Occasionally, you would pull away to give it a brief lick or a kiss. Meanwhile, your hand continued to play with her other one, combining the pleasure into one unique sensation.</p><p>Vera let out a light moan as your hand and your mouth switched places, repeating the same motions. "Good girl," she whispered, stroking your hair. "Keep going."</p><p>You did as you were told, licking and kissing and sucking like your life depended on it. She tasted so good; you swore you could get addicted to her taste if she let you do this more often. Very rarely did she ever feel comfortable letting you touch her breasts. Again, you were grateful to her for allowing you to do this.</p><p>But, as per usual, she never let you do this for long. With a small tug on your hair, she said, "Okay, that's enough," and you pulled away obediently.</p><p>"Now, what do you say?" she prompted.</p><p>"Thank you, Master."</p><p>"Good girl," she repeated. "Now, get on the bed, ass up. I'll take off the skirt by myself."</p><p>Your heart raced with excitement as you followed her orders, getting into position on the bed. You peeked around to your side to watch her remove her skirt and felt a surge of arousal to see that she hadn't been wearing any underwear.</p><p>"Surprised?" she teased. "I told you, I know all your fetishes, even the tame ones."</p><p>You swallowed hard as you watched her slide the strap on, your gaze temporarily resting on her dripping pussy. How had you not noticed it before? Was she just better at hiding it then you were? That was probably the case. Vera had always been one to conceal any emotions other than rage and superiority.</p><p>She groaned ever so slightly as the harness went underneath her pussy, causing some more of her juices to leak out around it. Oh, yes, she was definitely very turned on - possibly just as turned on as you were. Even though the strap wasn't double-sided, the way it tightly fit around her cunt would be enough to give her pleasure while she fucked you.</p><p>Your reflections didn't last long, however, as your gaze eventually rested on the long, thick green cock that was attached to the front of the harness. It almost matched the color of her skin, though it was just a tad darker. You didn't care, though; it looked beautiful on her, and it fit her so well.</p><p>"You want it?" she purred, opening one of the drawers in the bedside table. From it, she produced a bottle of lube, from which she squeezed a generous amount onto her palm. She stood in front of you, stroking her cock with her lube-soaked hand. "Beg. Beg for my cock inside you."</p><p>You spoke up, your voice trembling. "Please...please, Master, I need your cock. I need it inside me, Master, please."</p><p>Vera rolled her eyes. "You call that begging? Please. Try harder, and maybe I'll consider it."</p><p>You sucked in a breath, swallowing down the last of your pride. "I just...please, Master, I need it, I've been waiting for so long...fuck me, Master, please? Take me, make me yours, please, please, pl- ah!"</p><p>You felt sharp nails running down your back as Vera got behind you, still not entering you like you wanted. "I said you can do better. Don't disappoint me, or you won't get anything at all."</p><p>Worry shot through your veins, and you practically buried your face into the pillow to keep yourself from screaming. "Please, Master, please, fuck me, slide your cock inside me and make me cum, please, I need it, I need you so badly, I'll do anything, <em>anything,</em> I'll be good, I'll be good, I just need your cock right now, please??" You paused before adding hastily, "If you do, I'll scream your name for you, I promise!"</p><p>Vera's mouth curled into a grin, and she let out a low growl of satisfaction. "That's more like it," she hissed, and without warning, she slid inside you, prompting a loud cry to erupt from your throat.</p><p>You went to bury your face in the pillow again, but Vera grabbed your hair and yanked your head up forcefully. "No," she said, "you're going to keep your head up and you're going to fucking take it, understand?"</p><p>You tried to nod, but it was difficult with a fistful of your hair in Vera's hand. Instead, you released a low, steady moan as she pounded into you, not relenting for a second. Vera fucked you hard and fast, her nails digging into your back hard enough to draw blood.</p><p>You let out a squeal of both pleasure and pain. Somehow, the two mixed together to create an incredible feeling that only added to the one between your legs, and soon enough your moans turned to screams while her cock slid in and out, in and out, in and out.</p><p>"You like that?" Her voice was low and fierce, sounding almost primal. "You love my cock, don't you? You fucking - <em>ah</em> - love that shit, huh?"</p><p>You could only gasp and moan in response. The sound of her words becoming more and more frenzied was enough to drive you wild all on its own.</p><p>"<em>Fuck,</em>" she muttered, "you're so fucking tight, you know that? G-god, it's..." Whatever she was about to say next was replaced by a barely-stifled grunt. She continued to slam into you, never loosening her grip on your hair, never lessening the force of her nails against your soft flesh.</p><p>"Master," you cried, "oh, Master, Master, Master, <em>Vera!</em>"</p><p>She groaned, her thrusts increasing in speed and force. You could tell by the way her breath hitched that she was getting close, and you were, too.</p><p>"Vera, Master, please," you pleaded, somehow managing to get the words out despite your scrambled brain, "can I cum, please? Please, can I cum?"</p><p>"Yeah," Vera huffed, "do it, do it, cum for your master." She inhaled sharply, murmuring curses and biting her lip.</p><p>The sight of her trying to contain her orgasm only served to speed up yours. With a scream, you came, shouting Vera's name over and over again. She didn't slow down in the slightest, which only caused even more of your juices to flow out.</p><p>"That's right!" Her voice was practically raised to the same level as yours. "I'm your master, I'm your superior, I'm...I'm g-gonna...!"</p><p>She didn't have to finish her sentence. Within seconds, she came, too, her thrusts gradually slowing as her fluids leaked out behind the harness. Only when she was completely finished did she come to a halt, her breath coming out in ragged pants.</p><p>Slowly, you raised your hips so that the toy could slide out of you with a wet popping sound. You turned onto your back to look up at Vera, still dazed from her own orgasm. You reached an arm out toward her, which she accepted.</p><p>"I love you," you whispered, stroking her cheek with your other hand. When she came to her senses, she smiled down at you and gave you a soft kiss on the lips.</p><p>"I love you, too," she replied. "Thank you for...indulging in this fantasy of mine."</p><p>You pulled her closer so that she was lying down beside her. "No problem! It was super fun! I like it when you get all bossy." You snickered a bit, rubbing her scaly hair and listening to her snakes hiss happily. "Well, bossier than usual."</p><p>"Oh, hush." She planted a kiss on your neck. "You're lucky you're my lover, or I would have you murdered for that comment."</p><p>"Oh, I'm <em>very</em> lucky, and not just because you haven't killed me yet." You pulled her chin up to kiss her lips again, loving the way they tasted. She always wore the same lipstick, but something about kissing her felt different and special every time.</p><p>"Whatever," she remarked when you broke apart, trying to hide her blush. "Just shut up and go to the bathroom or something. You look filthy."</p><p>"Yes, ma'am." You got up and stretched, gazing down at your girlfriend adoringly. You really were lucky to have someone as amazing as her.</p><p>"So..." you began before heading into the bathroom, "how about that threesome with Dahlia?"</p><p>She waved her hand at you, ushering you out of the room. "What part of 'shut up' don't you understand? I'm tired." Though she tried to sound annoyed, it was clear from one look at her face that she was amused.</p><p>"Okay, okay!" You rolled your eyes. "Whatever you say, <em>Master.</em>"</p><p>As you left to go get freshened up, you couldn't help but notice the pleasurable shudder that last comment seemed to send through her. With one last glance at her relaxed body, you left the room, wondering what other fun games your girlfriend would have in store next time.</p>
  </div><div class="fff_chapter_notes fff_foot_notes"><b>Author's Note:</b><blockquote class="userstuff"><p>im so fucking sorry for exposing myself like this i just........want to fuck the snake lady</p></blockquote></div></div>
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